Luxury Vacation Home Rentals on Anna Maria Island

Discover our Anna Maria Island vacation rentals with private pools, perfect for relaxing getaways with family, friends, or pets. From Anna Maria to Holmes Beach, Bradenton Beach, & right Off Island, our homes offer privacy, comfort, and easy access to the island’s best beaches, shops, and restaurants.

Our local team is here to ensure a seamless stay, offering personalized support and insider tips to make your vacation unforgettable. Whether you’re bringing your pup  or planning a family retreat, you’ll find the ideal home for your island escape.

Properties Available 39 properties available
Welcome to Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Set on a quiet street near the sand, Mango Bay blends open interiors with plenty of outdoor living. Upstairs, the main living floor brings kitchen, dining, and lounge spaces together
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Mango Bay
Mango Bay
Holmes Beach
$333.00 - $1,016.40 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 (6)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere calm meets connection, Serenity Now offers spacious living, modern comforts, and a private backyard oasis with a heated pool. Thoughtfully designed for ease and bal
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Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$342.00 - $1,128.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (13)
Welcome to Vela Mar!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceVela Mar is where elevated coastal living meets modern luxury innovation. Designed with intention and inspired by the sophistication of Miami-style smart living, this fully i
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Vela Mar
Vela Mar
Holmes Beach Pet Friendly
$333.00 - $1,386.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.Nestled on the peaceful North End of Anna Maria Island, just 500 feet f
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Anna Maria Aloha
Anna Maria Aloha
Anna Maria Pet Friendly
$230.85 - $819.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (13)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
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Tern Key
Tern Key
Anna Maria
$729.00 - $2,677.50 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (13)
Welcome to The Curated Palm!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceThe Curated Palm is a home that feels at once elevated and effortless — where thoughtful craftsmanship, inspired design, and island living align in perfect h
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The Curated Palm
The Curated Palm
Anna Maria
$640.00 - $2,782.50 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (11)
Welcome to Sandy Pants!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere creativity meets coastal calm, Sandy Pants brings modern design and island ease together just steps from the Gulf. Every detail feels intentional — from the na
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Sandy Pants
Sandy Pants
Holmes Beach
$315.00 - $1,042.80 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (41)
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
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The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$234.00 - $903.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (14)
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
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Sunset Margarita
Sunset Margarita
Off Island Pet Friendly
$161.50 - $525.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience AMI Peppertree Paradise — a light-filled beach home where mornings begin with salt air and end beneath the glow of island skies.Just three houses from th
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AMI Peppertree Paradise
AMI Peppertree Paradise
Anna Maria
$307.80 - $950.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (9)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceSet between the Gulf of Mexico and the Intracoastal Waterway, Mariner’s Crossing offers balance — connection and privacy, activity and calm. With
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$800.00 - $3,300.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (15)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
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Sol Mate
Sol Mate
Anna Maria Pet Friendly
$315.90 - $1,010.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (14)

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When is the best time to visit Anna Maria Island?

Anna Maria Island is beautiful any time of year, but different seasons are best for different activities. Spring and fall both have warm temperatures and fewer crowds, and are perfect for a more relaxed vacation spent enjoying the outdoors and checking out local attractions. Summer is the hottest and busiest time of year. If you’re looking for exciting summer energy, summer is your best bet. Winter in Anna Maria Island has cooler temperatures and the lowest prices.

Are dogs allowed on the beaches in Anna Maria Island?

Most of the beaches on Anna Maria Island do not allow dogs, so it’s important to check the regulations before bringing your pup. But even if you can’t bring your four-legged family member to one of the main beaches, there are plenty of alternatives, like Palma Sola Causeway Park & Bayfront Park. View Pet Friendly Rentals in Anna Maria Island.

What are the best beaches on Anna Maria Island?

Every beach on the island is fantastic! We love Bean Point, on the northern tip of the island, for its views, wildlife viewing, and spectacular shelling. Bradenton Beach is great for anyone looking for a mix of relaxation and activities, with easy access to biking trails and restaurants. And Holmes Beach is lovely for anyone who wants to swim in clear waters or relax in the sugar-soft sands the island is famous for. Rentals within walking distance to the beach

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